Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C62H86N12O16 |
Molecular Weight | 1255.4194 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@]1([H])C(=O)N2CCC[C@@]2([H])C(=O)N(C)CC(=O)N(C)[C@@]([H])(C(C)C)C(=O)O[C@]([H])(C)[C@@]([H])(C(=N1)O)N=C(c3ccc(C)c4c3nc-5c(c(c(=O)c(C)c5o4)N)C(=N[C@@]6([H])[C@@]([H])(C)OC(=O)[C@]([H])(C(C)C)N(C)C(=O)CN(C)C(=O)[C@]7([H])CCCN7C(=O)[C@@]([H])(C(C)C)N=C6O)O)O
InChI
InChIKey=RJURFGZVJUQBHK-IIXSONLDSA-N
InChI=1S/C62H86N12O16/c1-27(2)42-59(84)73-23-17-19-36(73)57(82)69(13)25-38(75)71(15)48(29(5)6)61(86)88-33(11)44(55(80)65-42)67-53(78)35-22-21-31(9)51-46(35)64-47-40(41(63)50(77)32(10)52(47)90-51)54(79)68-45-34(12)89-62(87)49(30(7)8)72(16)39(76)26-70(14)58(83)37-20-18-24-74(37)60(85)43(28(3)4)66-56(45)81/h21-22,27-30,33-34,36-37,42-45,48-49H,17-20,23-26,63H2,1-16H3,(H,65,80)(H,66,81)(H,67,78)(H,68,79)/t33-,34-,36+,37+,42-,43-,44+,45+,48+,49+/m1/s1
Molecular Formula | C62H86N12O16 |
Molecular Weight | 1255.4194 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1734954
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1734954
Dactinomycin (actinomycin D) was isolated from Streptomyces by Selman Waksman in 1940s. The antibiotic shows anti-cancer activity; it was approved by FDA for the treatment of different cancer conditions among which are Ewing's sarcoma, Wilm's tumor, gestational trophoblastic disease, etc. Dactinomycin exerts its action by binding to DNA (preferably to GC motif) and thus inhibiting transcription.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 |
156.25 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | COSMEGEN Approved UseCOSMEGEN, as part of a combination chemotherapy and/or multi-modality treatment regimen, is indicated for the treatment of Wilms’ tumor, childhood rhabdomyosarcoma, Ewing’s sarcoma and metastatic, nonseminomatous testicular cancer. COSMEGEN is indicated as a single agent, or as part of a combination chemotherapy regimen, for the treatment of gestational trophoblastic neoplasia. COSMEGEN, as a component of regional perfusion, is indicated for the palliative and/or adjunctive treatment of locally recurrent or locoregional solid malignancies. Launch Date-1.59667192E11 |
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Primary | COSMEGEN Approved UseCOSMEGEN, as part of a combination chemotherapy and/or multi-modality treatment regimen, is indicated for the treatment of Wilms’ tumor, childhood rhabdomyosarcoma, Ewing’s sarcoma and metastatic, nonseminomatous testicular cancer. COSMEGEN is indicated as a single agent, or as part of a combination chemotherapy regimen, for the treatment of gestational trophoblastic neoplasia. COSMEGEN, as a component of regional perfusion, is indicated for the palliative and/or adjunctive treatment of locally recurrent or locoregional solid malignancies. Launch Date-1.59667192E11 |
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Primary | COSMEGEN Approved UseCOSMEGEN, as part of a combination chemotherapy and/or multi-modality treatment regimen, is indicated for the treatment of Wilms’ tumor, childhood rhabdomyosarcoma, Ewing’s sarcoma and metastatic, nonseminomatous testicular cancer. COSMEGEN is indicated as a single agent, or as part of a combination chemotherapy regimen, for the treatment of gestational trophoblastic neoplasia. COSMEGEN, as a component of regional perfusion, is indicated for the palliative and/or adjunctive treatment of locally recurrent or locoregional solid malignancies. Launch Date-1.59667192E11 |
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Primary | COSMEGEN Approved UseCOSMEGEN, as part of a combination chemotherapy and/or multi-modality treatment regimen, is indicated for the treatment of Wilms’ tumor, childhood rhabdomyosarcoma, Ewing’s sarcoma and metastatic, nonseminomatous testicular cancer. COSMEGEN is indicated as a single agent, or as part of a combination chemotherapy regimen, for the treatment of gestational trophoblastic neoplasia. COSMEGEN, as a component of regional perfusion, is indicated for the palliative and/or adjunctive treatment of locally recurrent or locoregional solid malignancies. Launch Date-1.59667192E11 |
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Primary | COSMEGEN Approved UseCOSMEGEN, as part of a combination chemotherapy and/or multi-modality treatment regimen, is indicated for the treatment of Wilms’ tumor, childhood rhabdomyosarcoma, Ewing’s sarcoma and metastatic, nonseminomatous testicular cancer. COSMEGEN is indicated as a single agent, or as part of a combination chemotherapy regimen, for the treatment of gestational trophoblastic neoplasia. COSMEGEN, as a component of regional perfusion, is indicated for the palliative and/or adjunctive treatment of locally recurrent or locoregional solid malignancies. Launch Date-1.59667192E11 |
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Palliative | COSMEGEN Approved UseCOSMEGEN, as part of a combination chemotherapy and/or multi-modality treatment regimen, is indicated for the treatment of Wilms’ tumor, childhood rhabdomyosarcoma, Ewing’s sarcoma and metastatic, nonseminomatous testicular cancer. COSMEGEN is indicated as a single agent, or as part of a combination chemotherapy regimen, for the treatment of gestational trophoblastic neoplasia. COSMEGEN, as a component of regional perfusion, is indicated for the palliative and/or adjunctive treatment of locally recurrent or locoregional solid malignancies. Launch Date-1.59667192E11 |
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Palliative | COSMEGEN Approved UseCOSMEGEN, as part of a combination chemotherapy and/or multi-modality treatment regimen, is indicated for the treatment of Wilms’ tumor, childhood rhabdomyosarcoma, Ewing’s sarcoma and metastatic, nonseminomatous testicular cancer. COSMEGEN is indicated as a single agent, or as part of a combination chemotherapy regimen, for the treatment of gestational trophoblastic neoplasia. COSMEGEN, as a component of regional perfusion, is indicated for the palliative and/or adjunctive treatment of locally recurrent or locoregional solid malignancies. Launch Date-1.59667192E11 |
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Palliative | COSMEGEN Approved UseCOSMEGEN, as part of a combination chemotherapy and/or multi-modality treatment regimen, is indicated for the treatment of Wilms’ tumor, childhood rhabdomyosarcoma, Ewing’s sarcoma and metastatic, nonseminomatous testicular cancer. COSMEGEN is indicated as a single agent, or as part of a combination chemotherapy regimen, for the treatment of gestational trophoblastic neoplasia. COSMEGEN, as a component of regional perfusion, is indicated for the palliative and/or adjunctive treatment of locally recurrent or locoregional solid malignancies. Launch Date-1.59667192E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1667253 |
3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DACTINOMYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
25.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16115931 |
1.1 mg/m² unknown, intravenous dose: 1.1 mg/m² route of administration: Intravenous experiment type: UNKNOWN co-administered: |
DACTINOMYCIN plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
142.4 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1667253 |
3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DACTINOMYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.67 μg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16115931 |
1.1 mg/m² unknown, intravenous dose: 1.1 mg/m² route of administration: Intravenous experiment type: UNKNOWN co-administered: |
DACTINOMYCIN plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1667253 |
3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DACTINOMYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
28.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16115931 |
1.1 mg/m² unknown, intravenous dose: 1.1 mg/m² route of administration: Intravenous experiment type: UNKNOWN co-administered: |
DACTINOMYCIN plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1667253 |
3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DACTINOMYCIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.15 mg/kg 1 times / day multiple, intravenous Overdose Dose: 0.15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 0.15 mg/kg, 1 times / day Sources: |
unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: |
Other AEs: Pancytopenia, Mucositis... Other AEs: Pancytopenia (1 patient) Sources: Mucositis (severe, 1 patient) Pancreatitis (1 patient) Hyponatremia (1 patient) Hypocalcemia (1 patient) Respiratory distress (1 patient) Melena (1 patient) |
0.15 ug/kg multiple, intravenous (total) Highest studied dose Dose: 0.15 ug/kg Route: intravenous Route: multiple Dose: 0.15 ug/kg Sources: |
unhealthy, 40-77 years n = 2 Health Status: unhealthy Condition: malignant melanoma Age Group: 40-77 years Sex: F Population Size: 2 Sources: |
|
1.5 mg/m2 single, intravenous Highest studied dose Dose: 1.5 mg/m2 Route: intravenous Route: single Dose: 1.5 mg/m2 Sources: |
unknown, children n = 1 Health Status: unknown Age Group: children Population Size: 1 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypocalcemia | 1 patient | 0.15 mg/kg 1 times / day multiple, intravenous Overdose Dose: 0.15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 0.15 mg/kg, 1 times / day Sources: |
unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: |
Hyponatremia | 1 patient | 0.15 mg/kg 1 times / day multiple, intravenous Overdose Dose: 0.15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 0.15 mg/kg, 1 times / day Sources: |
unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: |
Melena | 1 patient | 0.15 mg/kg 1 times / day multiple, intravenous Overdose Dose: 0.15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 0.15 mg/kg, 1 times / day Sources: |
unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: |
Pancreatitis | 1 patient | 0.15 mg/kg 1 times / day multiple, intravenous Overdose Dose: 0.15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 0.15 mg/kg, 1 times / day Sources: |
unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: |
Pancytopenia | 1 patient | 0.15 mg/kg 1 times / day multiple, intravenous Overdose Dose: 0.15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 0.15 mg/kg, 1 times / day Sources: |
unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: |
Respiratory distress | 1 patient | 0.15 mg/kg 1 times / day multiple, intravenous Overdose Dose: 0.15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 0.15 mg/kg, 1 times / day Sources: |
unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: |
Mucositis | severe, 1 patient | 0.15 mg/kg 1 times / day multiple, intravenous Overdose Dose: 0.15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 0.15 mg/kg, 1 times / day Sources: |
unhealthy, 18 months n = 1 Health Status: unhealthy Age Group: 18 months Sex: M Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Inhibition of VCAM-1 expression in human bronchial epithelial cells by glucocorticoids. | 1999 Apr |
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Rapid nucleolytic degradation of the small cytoplasmic Y RNAs during apoptosis. | 1999 Aug 27 |
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Actinomycin D and staurosporine, potent apoptosis inducers in vitro, are potentially effective chemotherapeutic agents against glioblastoma multiforme. | 2000 |
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Testin induction: the role of cyclic 3',5'-adenosine monophosphate/protein kinase A signaling in the regulation of basal and lonidamine-induced testin expression by rat sertoli cells. | 2000 Dec |
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Experimental model of hepatic venoocclusive disease (VOD) caused by dactinomycin--preliminary report about hepatoprotective effect of amifostine. | 2000 May-Jun |
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Venoocclusive liver disease (VOD) as a complication of Wilms' tumour management in the series of consecutive 206 patients. | 2000 Oct |
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Modification of biophysical properties of lung epithelial Na(+) channels by dexamethasone. | 2000 Sep |
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Stimulation of cyclooxygenase-2-activity by nitric oxide-derived species in rat chondrocyte: lack of contribution to loss of cartilage anabolism. | 2001 Apr 15 |
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Nitric oxide suppresses the expression of Bcl-2 binding protein BNIP3 in hepatocytes. | 2001 Dec 14 |
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Transient posterior encephalopathy induced by chemotherapy in children. | 2001 Feb |
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Combination of tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) and actinomycin D induces apoptosis even in TRAIL-resistant human pancreatic cancer cells. | 2001 Feb |
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The effects of particulate wear debris, cytokines, and growth factors on the functions of MG-63 osteoblasts. | 2001 Feb |
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Differential induction of stearoyl-CoA desaturase and acyl-CoA oxidase genes by fibrates in HepG2 cells. | 2001 Feb 1 |
|
Developmental reprogramming of rat GLUT-5 requires de novo mRNA and protein synthesis. | 2001 Jan |
|
Arsenic induces expression of the multidrug resistance-associated protein 2 (MRP2) gene in primary rat and human hepatocytes. | 2001 Jul |
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Cadmium-induced cell transformation and tumorigenesis are associated with transcriptional activation of c-fos, c-jun, and c-myc proto-oncogenes: role of cellular calcium and reactive oxygen species. | 2001 Jun |
|
Differential induction of rat hepatic cytochromes P450 3A1, 3A2, 2B1, 2B2, and 2E1 in response to pyridine treatment. | 2001 Mar |
|
Gene expression profile in BALB/c-3T3 cells transformed with beryllium sulfate. | 2001 Sep |
|
The histone deacetylase inhibitor and chemotherapeutic agent suberoylanilide hydroxamic acid (SAHA) induces a cell-death pathway characterized by cleavage of Bid and production of reactive oxygen species. | 2001 Sep 11 |
|
Changes in gene expression linked to methamphetamine-induced dopaminergic neurotoxicity. | 2002 Jan 1 |
|
Identification of manganese superoxide dismutase as a NO-regulated gene in rat glomerular mesangial cells by 2D gel electrophoresis. | 2003 Dec |
|
Potent iron chelators increase the mRNA levels of the universal cyclin-dependent kinase inhibitor p21(CIP1/WAF1), but paradoxically inhibit its translation: a potential mechanism of cell cycle dysregulation. | 2003 Jun |
|
Synergy between sulforaphane and selenium in the induction of thioredoxin reductase 1 requires both transcriptional and translational modulation. | 2003 Mar |
|
Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes. | 2003 Mar |
|
Leptin induces increased alpha2(I) collagen gene expression in cultured rat hepatic stellate cells. | 2003 May 15 |
|
Effects of hypoxia on monocyte inflammatory mediator production: Dissociation between changes in cyclooxygenase-2 expression and eicosanoid synthesis. | 2003 Oct 3 |
|
Thyroid hormone activates fibroblast growth factor receptor-1 in bone. | 2003 Sep |
|
Morphine suppresses lymphocyte apoptosis by blocking p53-mediated death signaling. | 2003 Sep 5 |
|
Troglitazone inhibits cyclin D1 expression and cell cycling independently of PPARgamma in normal mouse skin keratinocytes. | 2004 Dec |
|
Veno-occlusive disease in pediatric patients receiving actinomycin D and vincristine only for the treatment of rhabdomyosarcoma. | 2004 Dec |
|
DEP-induced fra-1 expression correlates with a distinct activation of AP-1-dependent gene transcription in the lung. | 2004 Feb |
|
Mechanism of heme oxygenase-1 gene induction by quercetin in rat aortic smooth muscle cells. | 2004 Jun |
|
Endosulfan-mediated biochemical changes in the freshwater fish Clarias batrachus. | 2004 Mar |
|
Immune-mediated thrombocytopenia following dactinomycin therapy in a child with alveolar rhabdomyosarcoma: the unresolved issues. | 2004 Nov |
|
2-Substituted benzoxazinone analogues as anti-human coronavirus (anti-HCoV) and ICAM-1 expression inhibition agents. | 2004 Sep 20 |
|
Establishment and characterization of new cellular lymphoma model expressing transgenic human MDR1. | 2005 Apr |
|
Mechanisms of thymidine kinase/ganciclovir and cytosine deaminase/ 5-fluorocytosine suicide gene therapy-induced cell death in glioma cells. | 2005 Feb 10 |
|
Induction of thioredoxin reductase as an adaptive response to acrolein in human umbilical vein endothelial cells. | 2005 Feb 25 |
|
Mechanism of concentration-dependent induction of heme oxygenase-1 by resveratrol in human aortic smooth muscle cells. | 2005 Jan 1 |
|
Activation of peroxisome proliferator-activated receptor alpha increases the expression and activity of microsomal triglyceride transfer protein in the liver. | 2005 Jan 14 |
|
Differential regulation of chemokine expression by peroxisome proliferator-activated receptor gamma agonists: interactions with glucocorticoids and beta2-agonists. | 2005 Jan 28 |
|
Mechanism of TNF-{alpha} modulation of Caco-2 intestinal epithelial tight junction barrier: role of myosin light-chain kinase protein expression. | 2005 Mar |
|
Mitochondrial redox state regulates transcription of the nuclear-encoded mitochondrial protein manganese superoxide dismutase: a proposed adaptive response to mitochondrial redox imbalance. | 2005 Mar 1 |
|
Promoting insulin secretion in pancreatic islets by means of bisphenol A and nonylphenol via intracellular estrogen receptors. | 2005 May |
Patents
Sample Use Guides
Wilms’ Tumor, Childhood Rhabdomyosarcoma and Ewing’s Sarcoma: Regimens of 15 mcg/kg intravenously daily for five days administered in various combinations and schedules with other chemotherapeutic agents; Metastatic Nonseminomatous Testicular Cancer: 1000 mcg/m2 intravenously on Day 1 as part of a combination regimen with cyclophosphamide, bleomycin, vinblastine, and cisplatin; Gestational Trophoblastic Neoplasia: 12 mcg/kg intravenously daily for five days as a single agent. 500 mcg intravenously on Days 1 and 2 as part of a combination regimen with etoposide, methotrexate, folinic acid, vincristine, cyclophosphamide and cisplatin; Regional Perfusion in Locally Recurrent and Locoregional Solid Malignancies: 50 mcg (0.05 mg) per kilogram of body weight for lower extremity or pelvis, 35 mcg (0.035 mg) per kilogram of body weight for upper extremity.
Route of Administration:
Intravenous
Human osteosarcoma cell line MG63 were incubated with dactinomycin (actinomycin D) at final concentrations of 0.1, 0.5, 1 and 5 uM during 0, 2, 6 and 24 hours. The drug was shown to inhibit the proliferation of cells by decreasing cyclin gene transcriptions.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 20:57:37 UTC 2021
by
admin
on
Fri Jun 25 20:57:37 UTC 2021
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Record UNII |
1CC1JFE158
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C204
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WHO-ESSENTIAL MEDICINES LIST |
8.2
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NDF-RT |
N0000000233
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LIVERTOX |
258
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IARC | Actinomycin D | ||
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NDF-RT |
N0000000150
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NDF-RT |
N0000180850
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WHO-ATC |
L01DA01
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WHO-VATC |
QL01DA01
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3220
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457193
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DB00970
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M4067
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PRIMARY | Merck Index | ||
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Dactinomycin
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SUB129914
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50-76-0
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1CC1JFE158
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C412
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200-063-6
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50-76-0
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DACTINOMYCIN
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PRIMARY | Description: An orange-red to red, crystalline powder.Solubility: Soluble in water at 10 ?C and slightly soluble in water at 37 ?C; freely soluble in ethanol (~750 g/l) TS and methanol R;very slightly soluble in ether R.Category: Cytotoxic drug.Storage: Dactinomycin should be kept in a tightly closed container, protected from light, and stored at a temperature notexceeding 40 ?C.Additional information: Dactinomycin is hygroscopic and is affected by light and heat.CAUTION: Dactinomycin must be handled with care, avoiding contact with the skin and inhalation of airborne particles. | ||
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SUB13528MIG
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1162400
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D003609
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CHEMBL1554
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1155
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3100
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PRIMARY | RxNorm | ||
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774
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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